The author of 《Psychotropic drugs. 18. Synthesis and structure-activity relations of 5-phenyl-1,3-dihydro-2H-thieno[2,3-e][1,4]diazepin-2-ones》 were Nakanishi, Michio; Tahara, Tetsuya; Araki, Kazuhiko; Shiroki, Masami; Tsumagari, Tatsumi; Takigawa, Yukio. And the article was published in Journal of Medicinal Chemistry in 1973. Category: amides-buliding-blocks The author mentioned the following in the article:
Several thienodiazepinones showed central nervous depressant activity in mice comparable to that of diazepam. One of the most active compounds, 5-o-fluorophenyl-7-ethyl-1,3-dihydro-2H-thieno[2,3-e][1,4]diazepin-2-one (I) [41191-07-5], inhibited fighting at 0.4 mg/kg orally and counteracted the lethal effects of pentetrazole at 0.3 mg/kg i.p. Some compounds, including I, also showed anticonvulsant, muscle-relaxant, and narcotic-potentiating activity in mice and a taming effect in olfactory bulbectomized rats. To synthesize I, o-fluoro-ω-cyanoacetophenone [31915-26-1] was condensed with butyraldehyde [123-72-8] and powd. S in DMF-NEt3 to form 2-amino-3-o-fluorobenzoyl-5-ethylthiophene [41191-09-7], converted to 2-chloroacetamido-3-o-fluorobenzoyl-5-ethylthiophene [41191-10-0] by reaction with ClCH2COCl, then to the iodoacetamido compound by exchange with NaI and to the aminoacetamido compound with NH3 gas, and cyclized by refluxing in pyridine-AcOH-C6H6. In the experiment, the researchers used 2-Amino-N-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)acetamide(cas: 50509-09-6Category: amides-buliding-blocks)
2-Amino-N-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)acetamide(cas: 50509-09-6) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Category: amides-buliding-blocks
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics